Hydrochloric Acid → HCID 86680204, compound

HRID 2402367Notes

Reaction equation

HRID 2402367 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:14]2[CH2:16][C:15]2([F:18])[F:17])[CH2:9][C:10]([O:12]C)=[O:11])=[CH:4][C:3]=1[NH:19][C:20](=[O:35])[C@H:21]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C@@H:22]([CH3:27])[C:23]([F:26])([F:25])[F:24].O.[OH-].[Li+].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:14]2[CH2:16][C:15]2([F:17])[F:18])[CH2:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[NH:19][C:20](=[O:35])[CH:21]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C@@H:22]([CH3:27])[C:23]([F:24])([F:25])[F:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86680205HCID 86680205, compound

Product 1

HCID 86680204HCID 86680204, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

114 mg (0.21 mmol) of methyl 3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)-3-(2,2-difluorocyclopropyl)propanoate (isomer 1; Example 124A) were dissolved in a mixture of 2 ml of dioxane and 1 ml of water, and 27 mg (0.64 mmol) of lithium hydroxide monohydrate were added. The mixture was stirred at RT overnight. The solution was then diluted with water and acidified with 1 N hydrochloric acid (pH about 2). The precipitated solid was filtered off with suction and dried under high vacuum overnight. This gave 89 mg (80% of theory) of the title compound as a diastereomer mixture in the form of a white solid.

Workup

  1. additionwere added
  2. filtrationThe precipitated solid was filtered off with suction
  3. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-76b5cf0836c549cd8ca0d11a99a06bf9
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

Loading…